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Everything You Need to Know About the Chester Cup

The Chester Cup is a handicap flat race that is the premier event of the Boodles May Festival at Chester Racecourse. The festival itself is a three-day affair that builds up to the running of the Chester Cup on the third day, also referred to as Chester Cup Day. In years prior, the Chester Cup was scheduled for the first day of the festival. Currently, it has a prestigious place on the final day, mainly due to its popularity and tendency to draw the largest crowd of the week. Inaugurated in 1824, this historic race is one of the most highly anticipated annual events at Chester Racecourse.

The Chester Cup

While this handicap flat race was initially open to horses aged three and older, its current minimum age is four. It is run on the Chester Cup Course which is a mile track that requires the runners to lap it twice and a quarter, as the race itself stretches 2 miles, 2 furlongs and 147 yards long. The field must turn left during the race, as the track is left-handed. The weight requirement for each horse is determined by a handicapper and is based on the perceived talent of each competitor.

fact file

location: Chester Racecourse

grade: Grade 1

race type: Flat (Handicap)

A Look at the History of the Chester Cup Handicap

The Chester Cup, currently referred to as the 188Bet Chester Cupafter its sponsor, was inaugurated in 1824 and initially referred to as the Chester Tradesman's Cup. In the early 19th century, handicaps were considered to be something of a novelty, and the Chester Cup only rose in prestige in 1836 when it was rumoured that a great sum of money was wagered on it (as much as £1 million).

By 1876, the Chester Cup was firmly ingrained as one of the most popular sporting holiday events in its region with a healthy attendance of around 100,000 people. Of course, while the modern day event is still anticipated as a Grade One race on the calendar, the attendance is much lower compared to a century ago.

The Chester Cup has been an annual event for almost 200 years and has rarely been cancelled in its long history. The most recent abandonment of this well-loved race was in 1983 when the track was flooded and subsequently waterlogged. The event resumed in 1984 after repairs. In 1994, the distance was extended by 70 yards.

The purse has hovered around the £100,000-£120,000 range for the past decade. Below are the winners from 2007 to present.


For nearly two centuries, the Chester Cup has been one of the most popular and unpredictable races held at Chester Racecourse. The current records for this handicap are listed below (as of 2017) .

  • Since its inaugural running in 1824, nine thoroughbreds have achieved double wins. These include Leamington (1857, 1859), Dalby (1865-1866), Pageant (1877-1888), Dare Devil (1892-1893), Chivalrous (1922-1923), Sea Pigeon (1977-1978), Top Cees (1995, 1997), Rainbow High (1999, 2001), and Anak Pekan (2004-2005).

  • Currently, the record for most wins of any jockey is a tie between Sam Darling and Lester Piggott. Each has four wins apiece from 1831 to 1839 and 1958 to 1976 respectively.

  • The trainer with the most wins is Barry Hills who won four times from Araphos in 1980, followed by a double win with Rainbow High in 1999 and 2001, then again in 2009 with Daraahem.

  • In 2001, Rainbow High set a new record as the winner carrying the heaviest weight (9st-13lbs) since Just David (9st-8lbs) in 1987.

Best Moments

A handicap always makes for a thrilling experience as the results are often unpredictable. Below are a couple of the best competitors and moments of the race (as of 2017) .

jockey racing horse
  • Willonyx is arguably one of the best winners of the Chester Cup since the early 19th century. Foaled in 1907, the stallion won not only the 1911 race, but several other prestigious events including the Basket Gold Cup, Cesarewitch, and Jockey Club Cup.

  • In the latter part of the 19th century and early 20th century, few favourites have won the Chester Cup. These include Mamlook (2010), Anak Pekan (2004), Rainbow High (1999), and Traveling Light (1990). That's only four favourites in the past four decades making for some of the most memorable moments in the race's history.